Plot: The (mis)adventures of Alvin, Simon, and Theodore continue with their manager/guardian Dave giving up songwriting to produce, so he can give them a more grounded life--but Alvin and the others love to perform. Dave has a new girlfriend, Samantha, whose son Miles treats them badly. Dave must go to Florida to help one of his artists, and he leaves the Chipmunks behind and takes Samantha. They think Dave plans to propose to her, and fear he'll ditch them. So they, along with Mitch, try to go to Florida to stop the proposal. But they don't have enough money, so the Chipmunks must ride in baggage, but when they're discovered, an air-marshal with a grudge against them decides to do away with them, so they force the plane to land. But they're far from Florida so they must go on foot.
Alternative Plot: Music manager Dave (Jason Lee) is not only enjoying a burgeoning career, but a blossoming romance with Samantha (Kimberly Williams-Paisley), a beautiful doctor who works in the emergency room. Through a series of misunderstandings, the chipmunks start to believe that a marriage proposal is on the horizon. Dreading the thought of an antagonistic stepbrother (Josh Green), Alvin (Justin Long), Theodore and Simon embark on a cross-country odyssey to prevent their best pal from ruining their lives.
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